IMPPAT Phytochemical information: 
O-sialic acid
O-sialic acid
Summary

SMILES: OC[C@H]([C@H]([C@@H]1O[C@](O)(C[C@@H]([C@H]1NC(=O)C)O)C(=O)O)O)O
InChI: InChI=1S/C11H19NO9/c1-4(14)12-7-5(15)2-11(20,10(18)19)21-9(7)8(17)6(16)3-13/h5-9,13,15-17,20H,2-3H2,1H3,(H,12,14)(H,18,19)/t5-,6+,7+,8+,9+,11+/m0/s1
InChIKey: SQVRNKJHWKZAKO-YRMXFSIDSA-N
DeepSMILES: OC[C@H][C@H][C@@H]O[C@]O)C[C@@H][C@H]6NC=O)C))))O)))C=O)O)))))O))O
Scaffold Graph/Node/Bond level: C1CCOCC1
Scaffold Graph/Node level: C1CCOCC1
Scaffold Graph level: C1CCCCC1
Functional groups: CC(=O)NC; CO; C[C@@](O)(OC)C(=O)O
Chemical classification
ClassyFire Kingdom: Organic compounds
ClassyFire Superclass: Organic oxygen compounds
ClassyFire Class: Organooxygen compounds
ClassyFire Subclass: Carbohydrates and carbohydrate conjugates
NP Classifier Biosynthetic pathway: Carbohydrates
NP Classifier Superclass: Aminosugars and aminoglycosides
NP Classifier Class: Aminosugars
Synonymous chemical names:
sialic acid
External chemical identifiers:
CID:444885; ChEMBL:CHEMBL1234621; ChEBI:49026; ZINC:ZINC000004081651; FDASRS:04A90EXP8V; SureChEMBL:SCHEMBL79085; MolPort-047-346-211
Chemical structure download
2D:2D MOL2D MOL22D SDF
3D:3D MOL3D MOL23D SDF3D PDB3D PDBQT
O-sialic acid
Physicochemical properties
Property name Tool Property value
Molecular weight (g/mol) RDKit 309.27
Log P RDKit -3.87
Topological polar surface area (Å2) RDKit 176.78
Number of hydrogen bond acceptors RDKit 8
Number of hydrogen bond donors RDKit 7
Number of carbon atoms RDKit 11
Number of heavy atoms RDKit 21
Number of heteroatoms RDKit 10
Number of nitrogen atoms RDKit 1
Number of sulfur atoms RDKit 0
Number of chiral carbon atoms RDKit 6
Stereochemical complexity RDKit 0.55
Number of sp hybridized carbon atoms RDKit 0
Number of sp2 hybridized carbon atoms RDKit 2
Number of sp3 hybridized carbon atoms RDKit 9
Shape complexity RDKit 0.82
Number of rotatable bonds RDKit 5
Number of aliphatic carbocycles RDKit 0
Number of aliphatic heterocycles RDKit 1
Number of aliphatic rings RDKit 1
Number of aromatic carbocycles RDKit 0
Number of aromatic heterocycles RDKit 0
Number of aromatic rings RDKit 0
Total number of rings RDKit 1
Number of saturated carbocycles RDKit 0
Number of saturated heterocycles RDKit 1
Number of saturated rings RDKit 1
Number of Smallest Set of Smallest Rings (SSSR) RDKit 1
O-sialic acid
Drug-likeness properties
Property nameToolProperty value
Number of Lipinski’s rule of 5 violations RDKit 1
Lipinski’s rule of 5 filter RDKit Passed
Number of Ghose filter violations RDKit 1
Ghose filter RDKit Failed
Veber filter RDKit Bad
Pfizer 3/75 filter RDKit Good
GSK 4/400 filter RDKit Good
Weighted quantitative estimate of drug-likeness (QEDw) score RDKit 0.2675
O-sialic acid
ADMET properties
Property nameToolProperty value
Bioavailability score SwissADME 0.11
Solubility class [ESOL] SwissADME Highly soluble
Solubility class [Silicos-IT] SwissADME Soluble
Blood Brain Barrier permeation SwissADME No
Gastrointestinal absorption SwissADME Low
Log Kp (Skin permeation, cm/s) SwissADME -10.65
Number of PAINS structural alerts SwissADME 0.0
Number of Brenk structural alerts SwissADME 0.0
CYP1A2 inhibitor SwissADME No
CYP2C19 inhibitor SwissADME No
CYP2C9 inhibitor SwissADME No
CYP2D6 inhibitor SwissADME No
CYP3A4 inhibitor SwissADME No
P-glycoprotein substrate SwissADME Yes
O-sialic acid
Predicted human target proteins
Protein identifierHGNC symbolCombined score from STITCH database
ENSP00000198536PILRA800
ENSP00000231461ST8SIA4849
ENSP00000233735REG1A800
ENSP00000254301LGALS3800
ENSP00000255040APCS800
ENSP00000256509CHL1922
ENSP00000263686SELP800
ENSP00000268164ST8SIA2913
ENSP00000271450FCGR2A800
ENSP00000284878CXADR800
ENSP00000292401AZGP1800
ENSP00000306099FGB800
ENSP00000306361FGA800
ENSP00000308938PLG800
ENSP00000309576LGALS8800
ENSP00000311153800
ENSP00000314151KLK3800
ENSP00000318472NCAM1896
ENSP00000320431ST8SIA3935
ENSP00000323328SIGLEC7800
ENSP00000331736SELE800
ENSP00000336829FGG800
ENSP00000341141SIGLEC1739
ENSP00000347714FCAR800
ENSP00000353720CES1800
ENSP00000356236SYT2795
ENSP00000378856LGALS9800
ENSP00000385834TF800
ENSP00000415200800
ENSP00000431254IGLL5800
The human target proteins were predicted using STITCH, a database of Chemical-Protein interaction networks.